The relation between the absolute stereochemistry of a series of acyclic alkylarylcarbinols and three groups of benzocycloalkenosls (1-indanols, 1-tetralols and seven- and eight-membered benzocycloalken-3-ols) and their elution order from a chiral HPLC column ("Pirkle") has shown that in the acyclic and seven- and eight-membered benzocycloalken-3-ols the enantiomers with an (structure omitted) configuration are preferentially retained by the column. While for 2-substituted 1-indanols and 1-tetralols the antipode is preferentially retained. In order to obtain these correlations it was necessary to prepare approximately fifty alcohols, enriched in one enantiomer whose configuration was either previously known or had to be established. These chiral alcohols were prepared using the microbial methods we had previously developed or are currently developing. Our correlations and theuse of a chiral HPLC column permit one to characterize and tentatively assign the absolute stereochemistry of nanogram quantities of related aromatic alcohols.